Here’s a quick guide to properly and successfully dressing for a first date.  Follow these tips and the only thing you have to do is NOT mess up by saying something stupid.


Look like you’ve made an effort, but not too much effort.
A man should look as if he had bought his clothes with intelligence, put them on with care and then forgotten all about them.  No woman wants to date a man who has spent more time getting ready than she has.

Buy a decent wallet.
Because all the brownie points you earn by paying for dinner will evaporate in an instant if your billfold says “Bad Motherfucker” on it.  Put your money into brown or black leather.  A money clip can be a stylish alternative as long as it isn’t in the shape of a dollar sign.

A logo T-shirt sends a message.

Not the right one.  This also applies to novelty socks, ties and anything with Stewie from Family Guy on it.


Because whether it’s before or after your eyes, backside and bank account, she will look and she will judge you by them – doesn’t matter who you are.  Good-quality leather lace-ups or loafers are the safest bets.  Socks are scarcely less important and should be fine wool or cashmere. Seriously, I really can’t emphasise this enough.  A female colleague’s grandma always told her never to trust a man with unpolished shoes.  Another is wary of men wearing shoes which are 
too polished. Yet another left a restaurant because her date was wearing flip-flops.  With a suit.  And don’t even think about mandals (man sandals).  You don’t live in a frat house so you shouldn’t dress like it, and if you do, by God move out now.

Keep your denim dark, slim and plain.

“Tricked-up” jeans will impress less than offering to go Dutch.  Also no bootcut unless you’re at the rodeo.

Wear a scent.

But not too much of it.  If you smell like a boudoir than she may suspect that you frequent one.  If in doubt, go classic and unassailably masculine.  The folks at Sephora (yes the girly perfume and makeup store) have created a touch screen app that shows you what cologne you might like based on what you already like.  Spray it on your chest and stomach under your shirt and on your hair to give her an incentive to get closer – wrists and neck wear off too quickly – and never down your trousers.  Also clean and trim your fingernails if you want to touch her – ever.

Sporting attire should be avoided at all costs

Unless your date involves watching or participating in a sport.  In which case there probably won’t be a second date.  Be a grown up and take her to dinner!

Dress for pleasure, not business.
Don’t wear a suit unless your date is somewhere incredibly swanky, and even then smart separates are almost always preferable.  As well as looking like you’ve come straight from work (and therefore made zero effort), if you’re dressed like a mobile phone salesman then it looks like you’re trying too aggressively to close the deal, and no respectable woman wants to get that vibe on the first date.

Good underwear.
Hell, the whole point of all of this is to eventually get down to your underwear and make a couple of bad decisions so Fruit of the Loom will just not cut it.  Regular boxers are just too grandpa-like, briefs are not my thing so I’ll never recommend it so go with a boxer brief.  It’s a good way to show off your manhood before the big reveal, and it’s just damn sexy. Spend a couple of dollars on some with a great cottony feel and maybe even a brand name or two.  You want your lady to shop at Cacique, Victoria’s Secret, and Frederick’s of Hollywood so why can’t you spend a couple of dollars to dress your package up in nice looking wrapping paper.   And well, because you never know…